Exchange 2016 and Outlook showing wrong name on SSL Cert

I am deploying an Exchange 2016 install onto a 2012 R2 server, and I keep running into an issue where Outlook keeps trying to point to the local name of the server, which throws up an SSL cert error. The server's real name is I am aware that having a *.com name for a local domain is not good policy, but that was the hand I was dealt. The Exchange 2016 is up and running, and hosting an email domain for The accounts propagate, send and receive email correctly. The public facing domain that points to the Exchange server is So the flow should go as follows:

(email dns hosted on godaddy) > (public) (dns hosted on godaddy )> public facing IP of server which our firewall NATs to the internal IP.

I have a SSL cert from DigiCert that includes the and SANs, and it is properly loaded onto the Exchange server. I can load up the OWA, and it shows it as a secure connection from I ran the Microsoft online tool, and after giving it all of the proper account information, it resolves everything just fine, using the SRV for autodiscover for the email domain, finding it routing to just fine, even giving a perfect SSL handshake along the way.

WHY then, does Outlook continue to point to the internal address of Which of course throws up the SSL cert error every time someone opens their outlook?

I have gone through and pointed every internal and external URL and URI to I have setup the split-DNS entries for the domain inside of my forest. I also checked the SCP in the Sites and Services of the domain, and that points to as it should.

NSLookups all resolve, both internally and externally to exactly where they are supposed to. DNS entries resolve to when pinging

Yet Outlook still pops up an SSL error saying it is trying to connect to WHY?

Also, if I login to an off-prem computer, and setup the Exchange account in Outlook using the 'connect by proxy' settings, the first time it connects, it will authenticate perfectly, giving no SSL errors. However, upon closing Outlook and re-opening, when it is trying to reconnect, it never does, because it changes the server it is trying to connect to back to the internal address.

First time:
User: first.last

Everytime after:
User: first.last

Outlook injects the local address of the server into the server information, even though the computer is not on-prem, meaning that the user can no longer connect to their mailbox!
Brendon GaigeIT DirectorAsked:
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Hypercat (Deb)Commented:
It sounds like it's your internal DNS records that aren't correct.  You need to add an autodiscover entry to your internal DNS to ensure the internal workstations find the correct name for that server.  Look at this article - it has instructions for configuring both external and internal DNS for Exchange 2016:
Brendon GaigeIT DirectorAuthor Commented:
So for my internal DNS I have it set as follows:

Forward Lookup Zones:
    autodiscover cname
    exchange cname
        _autodiscover SRV
    autodiscover Host(A)
    exchange HOST(A)
Reverse Lookup Zones: PTR PTR

What else am I supposed to put in? In every other case I test, it resolves the DNS to, except for Outlook.
viktor grantExchange ServersCommented:
HI Brendon,

The issue happens internally and externally?

Firstly you can try to solve internally. If you have the correct name in the certificate, you can create A record in order that the connection be quickly.

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Brendon GaigeIT DirectorAuthor Commented:
Viktor, I don't understand what you mean.

The issue happens both internally and externally, but only with Outlook.

I am trying to solve it internally. You can no longer put local names in public facing SSL certs per regulations. So how am I supposed to do that, when I have the public facing name in the cert, along with the public facing name listed in all public and local DNS, and it resolves correctly through every means except Outlook?
Brendon GaigeIT DirectorAuthor Commented:
Something is missing somewhere... It seems that Outlook makes two checks when attempting to connect to Exchange. I have been able to get it to resolve at times on the first check with the approved FQDN of but on the second check, it always returns the Why?
Brendon GaigeIT DirectorAuthor Commented:
Ok, so an update, I have been able to get Outlook to connect to Exchange, both internally and externally reliably. Once the connection is establish, Outlook updates the server information to show as:

Which is what it should show, and now atleast on the seeming first check, it will not ask for the SSL cert warning. It is however, now giving a pop-up after about 2-3 minutes of being connected saying the SSL cert does not recognize Why is it trying to connect to the address, when it has already established a correct connection with the address and created a secure connection?
Brendon GaigeIT DirectorAuthor Commented:
So, since no one else seemed to have any other suggestions. I seem to have resolved the issue on my own, by purchasing the SAN for my SSL cert for and adding it in. That seems to have stopped the SSL pop-ups. I don't feel like that was the 'actual and proper' way to resolve the issue, but it is working for the time being.

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Brendon GaigeIT DirectorAuthor Commented:
No other truly helpful options were presented.
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